The question is very simple. Who is the greatest heel of all time? When answering this question, also add what they're best feud was that made them as over a heel as they were. Now when asked this question many great names come to mind such as Shawn Michaels, Triple H, Hulk Hogan, Roddy Piper, Ted Dibiase, Chris Jericho, etc etc etc but my choice is... DRUM ROLL PLEASE... Ric Flair. WOOOOOOOOOOOOOOOOOOOOO!!!!!! Where do I begin, 16 world championships, leader of the 4 Horsemen, founding member of Evolution, the man has done it all. His feud with Dusty Rhodes was one of the greatest of all time and he could talk with the best of them. Maybe the greatest talker of all time, Flair is the clear winner here in my opinion and he is the wrestler that influenced many of the greatest wrestlers (and heels) of all time such as Randy Orton, Triple H, and Shawn Michaels. WOOOOOOOOOOOOOOOOOOOOO!!!! So, who's your choice? What was your choice's greatest feud? While answering your question remember one thing. WOOOOOOOOOOOOOOOOOO!!!!!!!!!

The better heels would be the ones that didn't repeatedly turn face and heel.

Flair was a great heel but didn't do much hellish stuff apart from cheating, compared to piper hitting Snuka with the coconut.

Well.... Flair did orchestrate the post match locker room beatdown of The Rock & Roll Express that saw him repeatedly knee drop Ricky Morton's face into the concrete floor while The Horsemen held down his partner Robert Gibson, making him watch (also rubbed the near comatose Morton's face in the concrete repeatedly, setting up an entire segment in their upcoming matches where Flair would rip out Morton's stitches and bandages, re attack the face, etc)... There was breaking Dusty Rhodes leg (Ironically after Dusty came to the ring TO SAVE Flair after a post match attack by The Russians following a Flair win over the hated "Russian Nightmare" Nikita Kolloff)... Not only alleging, but showing doctored photos, of his "affair" with Elizabeth (this lead to some of the best promos of all time as part of the "She was mine before she was your, she's damaged goods" fued with Randy Savage)... Stealing Liz away from Randy, then getting him suspended while going on a shopping spree with his money (courtesy of Liz) (Leading to those expensive champagne & caviar Ringside Buffett segments on Nitro, paid for by Savage)... ... Breaking Sting's knee in a Horsemen beatdown immediately after dumping him from the group... The parking lot beatdown on Lex Luger circa 1988... Dressing in drag to gain entrance into the arena to interferre in Savage & Hogan's matches while being banned from appearing at ringside circa 1995... Beating up Savage at ringside during his title match at SummerSlam 92 so he could defeat the injured Macho Man and win the World Title in 1992...

Hollywood Hogan, dude was such a hated heel at the time he turned, the nWo was so popular because of the outsiders but most if not all of thier heel heat cme from hogan, i just finished watching the matches on nWo revolution dvd and it really made me remember what a entertaining heel hogan was back then, just his body language and all the dirty tricks he pulled and the announcers hyping him up, greatest heel IMO

The Dirtiest Player in the game was called that for a reason. How many times did he have his henchmen come into the ring to beat his opponent down to save the title for him? The Brass knuckles, the pulling of the tights, and the backstage beatdowns were a huge part of Ric Flair. As a kid one of the main reasons I watched a WCW show was to see someone pin Flair. I remember them repeatedly banning the Horsemen from ringside only for them to interfere anyway. He was the guy I wanted to see get beat so bad, but dammit hardly anyone was ever able to do it. To me that is the definition of a heel.

Flair was a very good heel, and all the guys you already mentioned. But, the best heel is the one who legitimately scares the crap out of the crowd when he comes to wrestle. That won't happen anymore in this homogenized society we have now. The greatest heel I've ever seen is Ed Farhat, The Original Sheik. Any person who saw him wrestle in Japan, Detroit, Toronto, or Los Angeles who whole-heartedly agree with me. Especially, when you can be so villianous that you make the crowd cheer for Freddie Blassie. When you originate throwing fire at your opponents, or use a simple golf pencil to carve a roadmap in an opponent's head, you are a heel of the highest magnitude.

Good thread and I can't choose a winner but its between 3 contenders for me:

1 - Mr McMahon - As previous posters have said already, the guy was so easy to hate back in the Attitude Era! You always wanted to see Austin make a jackass out him in some way every week on Raw!

2 - Chris Jericho - Who else can turn heel without saying a word or attacking a face? I was really impressed with the 2012 return since he just simply trolled everyone! The best part of Jericho as a heel was when he turned into the self-honest man in a suit during 2008 and his rivalry with Shawn Michaels wasn't booked as just a typical Face vs Heel feud. He was such a hateable character who was able to great cut heel promos which is what you want from a heel!

3 - Triple H - "You're damn right it was me Shawn"! Triple H was one of the biggest faces if not the biggest face when he returned in Jan 2002 until he turned heel about 6 months later. The Shawn Michaels rivalry which lasted from 2002-2004 is probably my favourite of all time. Can cut excellent heel promos as well to go with any of his storylines! Even in 99 when he first turned into a main event heel, you could see why he was such a great heel and had the perfect storylines.